The intramolecular alkylation of several bromo- and epoxy-2-methylcyclopentenones, 18–23 and 33, are described. In all cases, except 33, alkylative cyclization occurs at the γ′ position to the conjoint ring systems 25–31. The "blocked" bromide 33 (γ′ geminal dimethyl substituent) cyclizes to the fused ring hydrindenones 35 and/or 34 depending upon conditions. Enolateanion generation from 3-ethyl-2-methyl-2-cyclopentenone (36) with various bases (KH, LDA, Et3N) is described and the anion populations determined by quenching with chlorotrimethylsilane to afford the enol ethers 39–41. The intramolecular alkylations are discussed.